Easier still is what I'll call the three steps forward three steps back method (see: non-technological methods in
Keystroke logging ).
Auto Form Filling would be nice but Auto Field filling would be sufficient.
I'd suggest that the Autohotkey program that does the field filling should first check whether "Dead man's switch" is present before executing. This would help prevent the use of the password by anyone other than the holder of the USB drive.
I hope someone (Skrommel perhaps?) has a go at this.
After I test the device and see that it works as intended I'd like to share part 3 of my project with everyone.